


Best Laid Plans

by Impala_Dreamer



Category: Supernatural
Genre: F/M, Fluff, Gratuitous Fluff. Smidge of Smut (Barely)
Language: English
Status: Completed
Published: 2021-02-18
Updated: 2021-02-18
Packaged: 2021-03-13 08:54:42
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,464
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29523939
Author URL: https://archiveofourown.org/users/Impala_Dreamer/pseuds/Impala_Dreamer
Summary: ~Dean tries to go all chick-flick on you but fails miserably~
Relationships: Dean/reader
Kudos: 11





	Best Laid Plans

“So any big plans for tonight?” Sam asked his brother as they both reached for the coffee pot at the same time.

Dean beat him to it and let out a victorious chuckle. “I don’t know what you’re referring to,” he lied; a mischievous sparkle overtaking his green eyes.

“Good morning!” Y/N appeared in the archway, bouncing into the kitchen and running to Dean. Careful to avoid the hot mug of joe in his hands, she leaned up on her toes to kiss him hello. Dean closed his eyes as her lips distracted him, so much so that he didn’t notice Y/N had stolen his coffee until she pulled back and took a sip.

“Hey!”

Y/N cringed. “You forgot the milk.”

“I did not. That was mine,” Dean laughed, watching her float over to the fridge with a smile. She was adorable, even right out of bed, especially right out of bed. Her hair was a mess of tangles and unruly slept-on waves, her eyes were bright but sleepy, and her voice was crackly and low. Also didn’t hurt that she looked hot as hell in his old t-shirt that hung down to her thighs, almost completely covering the tiny sleep shorts she wore.

“I would have thought you’d at least make me coffee this morning, Dean.” Y/N poured a splash of milk into the mug and turned to give Dean a chance to defend himself.

“You always make your own coffee,” he said with a shrug and went for another cup. Her sigh was not lost on him; he knew what she was talking about, but he had a plan.

“Yeah, but… I thought maybe… today…”

Again he shrugged, this time looking up at her, feigning ignorance. “It’s Wednesday. What’s the big deal?”

Her reaction was instant and made Dean feel a twinge of guilt. Maybe this wasn’t the best plan.

“Oh, well, alright then.” Y/N pushed away from the counter and nodded to Sam as she exited the kitchen, not giving Dean a second glance, or chance.

Sam made sure she was clear before spinning around to glare at Dean. “Are you serious?”

“What?” Dean raised his eyebrows over his mug as he took a seat.

“Dean, it’s your anniversary!” Sam was in shock, but not really. If anyone were to forget such a thing, it would be Dean. He didn’t exactly keep a calendar.

Dean rolled his eyes and shouted in a low whisper, “I know that!”

“So what the hell are you doing?”

Dean looked over his shoulder to make sure Y/N was really gone and not lingering in the hall. “I’m being… romantic. Like, chick-flick romantic.” Sam’s face scrunched in confusion, so Dean went on. “You know, guy forgets anniversary and has to make it up to the girl with a grand gesture. All that sappy shit.”

“So you’re planning to piss her off all day and then, what? Take her up in a hot air balloon and all is forgiven? Y/N’s not gonna be too happy about that.”

“She’s gonna love it, Sammy. She’s always saying we don’t do anything romantic. So here’s me pulling out all the romance. I’m gonna romance her so much she’ll beg me to stop.”

Sam shook his head and held up a hand for Dean to stop. “That’s too much info, no thank you.”

“Not like that, you perv. But…” Dean smirked, “Yeah, like that too.”

“You’re disgusting.” Sam cringed.

“And you’re jealous.” Dean wiggled his eyebrows and sat back, going over his plan. One year. He and Y/N had been together officially for one full year. That was a lifetime to him. He’d never been with anyone longer than a month, and even then, it was sporadic meetings and flyby loving. Y/N was different. He was in love, really for the first time, and he was going to show her in the most epic way possible. “Yeah, I got a plan.”

The day went on with Dean playing his part a little too well. Y/N dropped hint after hint and Dean ignored them all. He knew he was playing a dangerous game, but hoped it would be worth it. He wasn’t exactly the flowers and chocolate, scented candle romantic type, but if he pulled this off, it would surely make up for all the times he didn’t open the car door for her or pluck a flower from a passing garden just because.

By four o’clock, Y/N was done; aggravated and hurt that Dean had forgotten their special day. She knew it wasn’t his style, but a year was a long time. At first she thought maybe he was just messing with her, but after a while, her hope faded and she gave up entirely.

Tired and annoyed, she stood up from her place in the Library and announced her departure. “Well, I’m gonna go take a shower. Then I’ll start dinner I guess.” She paused and looked at Dean who was busy with his nose in a book. “Unless…?”

He barely looked up, but nodded towards her. “Yeah, dinner sounds good, babe.”

Y/N grit her teeth and pushed down a wave of disappointment. “OK. Great.”

Dean watched her walk off slowly, feeling a little guilty but very excited. He waited a good ten minutes before sneaking off to set up her room and enact his plan. Thankfully, Y/N took long showers so he wouldn’t be caught red-handed if he hurried.

Y/N shuffled sadly down the hallway, her heart a little broken; the droplets from her wet hair hiding her tears well. She knew she was being silly, shouldn’t have gotten her hopes up, but it was hard not to be upset. She didn’t know what she had expected, but she thought at least a “Happy anniversary, Princess” or two would have passed Dean’s lips at least once during the day.

“Oh, well,” she sighed to herself and opened her bedroom door, immediately gasping at the sight before her. From the threshold to the bed lay a trail of pink and red rose petals that converged on the bed, forming a heart around a large white box. Her lips pulled into an excited smile as she looked up and down the hallway, looking for Dean, but he was nowhere to be found. Carefully she walked in and rushed to the bed, looking down on the mysterious box. A white slip of paper sat on top, displaying two simple words in Dean’s heavy-handed scrawl: Wear Me.

She held the message in her hand for a long moment, fighting the urge to cry again, this time from relief and excitement. He hadn’t really forgotten, the jerk. When she opened the box, the tears did come. Inside was a beautiful black dress and a pair of strappy heels that she guessed, correctly, were just her size.

“I’m gonna kill him,” she said as she jumped up and down like a love-struck teenager.

After spending way too long in the mirror, marveling at how great the dress looked and making sure her makeup was perfect, Y/N made her way down the long hall, enjoying the click of her heels on the hard floor. She honestly couldn’t remember the last time she’d gotten so dressed up. Normally it was either flannel and jeans or drab business suits; this was fun.

When she emerged from the hall and stepped into the War Room, she was met with another sight that took her breath away. Waiting for her at the bottom of the stairs was the most handsome man she had ever seen.

Dean looked amazing in a new suit and tie. He was fresh from the shower, his chin smooth and hair perfect. The beautiful blue shirt he wore beneath the black jacket somehow made the emerald in his eyes glow brighter, and his smile stopped her heart. He held a single red rose in one hand, and hid the other behind his back, waiting patiently for her approach.

“You look… incredible,” she said, stopping just a few feet from him to truly take it all in.

“So do you,” he said sweetly as he handed her the rose. “But… you’re missing something.”

“Oh?” Y/N bit her lip, anxious to see what else he had up his sleeve.

Dean gave her a little smirk and revealed a blue velvet jewelry box that he held out, lifting the lid. “Happy anniversary, baby.”

Her smile was unstoppable, and the blood rose to her cheeks as she leaned forward to peek into the box. Inside, laid carefully on a bed of white satin, was a delicate silver chain with a bright green gem wrapped in a wire cage.

“Dean! It’s beautiful!”

“It’s peridot. For protection against… well, everything really, I guess. Just in case I can’t be there, which, I don’t really see happening, but…”

“It’s perfect, thank you.” Y/N gave him a brilliant smile and then reached out to run her hand down across the gem. As soon as she touched it, Dean slammed the lid shut in an attempt to startle her and make her laugh, but she yelped instead as the box crushed her fingers.

“Oh crap! Sorry!” Dean fumbled to open the lid and gave her the most pathetic face ever. “I’m so sorry. I was trying to do that thing-”

Y/N laughed. “Julia Roberts? Yeah, I got that,” she said as she stuck her finger in her mouth to soothe the sting.

“Sorry.”

“It’s OK, baby. Thank you for trying.” Y/N laughed again and pushed forward, laying her hand on his chest and drawing him down for a kiss. Dean’s distress faded away instantly, and he wrapped his arm around her back, pulling her in even closer.

His missteps did not end there. No matter what ridiculously romantic gesture Dean attempted, he somehow managed to fumble it. Holding the car door open was a success, but in closing it, he caught the hem of her dress, almost ripping it. The drive to the restaurant was without problem, but there was no parking anywhere, so he had to stash Baby three blocks away. When he helped Y/N out of the car, he let go of her hand too soon and she tripped a bit, turning her ankle slightly in the too-tall heels. Arm in arm, they made way down the street to dinner, but halfway there it began to rain, hard. And there was Dean, once again unprepared, without an umbrella, and by the time they reached their destination, they were soaked. Dean had even pulled out her chair, trying to play the gentleman, but ended up shoving her into the table as he pushed her in.

Y/N didn’t seem to mind any of his flubs, simply impressed that he was trying, but each mistake crushed Dean’s mood. He had planned everything so carefully, and it was all falling apart.

They ordered off of a menu that Dean could barely read, drank some fancy French wine that he had never heard of, and stared awkwardly at each other, feeling uncomfortable in the expensive restaurant. The only saving grace, as far as Dean was concerned, was how gorgeous Y/N looked. Her eyes sparkled in the candlelight and her smile was true. She was always perfect to him, but seeing her tonight, all dolled up, cemented in his heart that she was the most incredible woman he had ever seen.

When the food came, Dean stared down at his plate nervously. It was barely a meal. A tiny square of steak piled high with some kind of potato-like substance and a green twig thing. He lifted his fork, steeling his nerves before taking a bite, and cringed. When he looked up to check on Y/N, her face mimicked his, unsure of the food set before her.

“Uh, Dean? This is nice and all but…”

“You wanna get out of here?”

Y/N laughed. “God, yes.”

The rain had stopped, and the sky was clear; the storm clouds giving way to a bright moon and a sprinkling of stars. They parked by a lake and ate burgers on the hood of the car, laughing at Dean’s attempts at romance.

“You know, Dean, you don’t need to get all fancy with me. It was nice, but… that’s not really our style.” Y/N lay down against the windshield and reached for him, calling him to lay back with her.

“I know, I just wanted to do something special for you. A grand gesture, I guess.” He shrugged and looked up at the stars, feeling sorry for himself.

Y/N turned on her side and placed her hand on his cheek, turning his face towards her. “I do not need a grand gesture, Dean,” she said simply. “I love that you had this all planned, I do. But, I just need you. That’s all I ever need.”

Dean shifted, turning his body towards her and laying his hand in the curve of her waist. “Then you’re in luck, Princess. You got me.”

Dean found his romance in the press of her lips and the warmth of her skin. They kissed under the stars, pulling against each other’s mouths with greedy lips and searching tongues. Their hands moved slowly but freely, sneaking underneath the fancy clothes and pushing aside the pointless layers of confining fabric. When the flame reached its peak, Dean laid her down on the backseat, dropping down over her to worshiping every inch of her perfect skin. Over every bump and scar, every curve and dimple of soft flesh, he pressed a kiss. Her hands ran through his hair, tugging at the short strands as he claimed her with gentle hands that stretched her open, readying her for his love.

Dean rocked slowly into her, taking his time, drawing out the perfect moment that came on the heels of a less than perfect day. Flowers and candles and gifts were just things; things that Dean never got quite right. But this, pressed together, inch for inch, skin on skin, he got right. He showed her his love in the firm kisses that stole her breath. In the way he pushed her higher than anyone else ever could. In the way his heart beat fast and steady under her hand. In the strong arms he wrapped around her afterwards. In the whispered ‘I love you’s and the silent promise of a thousand more nights like this.

So maybe he wasn’t Richard Gere. Maybe he could never give her the rom-com life that he wanted to, but she didn’t care. She had everything she’d ever wanted, and Dean would make sure she had it as long as possible.


End file.
